The second migratory path followed by the runaways contrasted sharply with the urban migration. It led into the most remote, isolated backcountry, dense forests, bayous, swamps, or Indian territories. There, the fugitives formed maroon communities - organized enclaves of runaways-that developed in the earliest days and continued through abolition. As early as 1690, farmers in Harlem, New York, were complaining about the inhabitants of a maroon colony who were attacking the settlers.

The first known free black community in North America was a settlement of fugitive Africans called Gracia Real de Santa Teresa de Mose. Located near St. Augustine in Spanish Florida, it operated from 1739 to 1763.

The Origins of a Florida Sanctuary: Garcia Real de Santa Teresa de Mose , Chapter 2 from Black Society in Spanish Florida by Jane Landers

Some runaways established camps in Elliott's Cut, between the Ashepoo and Pon Pon rivers in South Carolina; and in the Indian nations of Alabama and Mississippi. In the eighteenth century, others had taken refuge in Spanish Florida with the Seminole Indians. Black and native Seminoles joined forces against the U.S. army during two wars in 1812 and 1835.  In 1822, the sub-agent for the Florida Indians wrote:

It will be difficult (says he) to form a prudent determination with respect to the ‘maroon negroes' (Exiles), who live among the Indians . . . . They fear being again made slaves, under the American Government, and will omit nothing to increase or keep alive mistrust among the Indians, whom they in fact govern. If it should become necessary to use force with them, it is to be feared that the Indians will take their part. It will, however, be necessary to remove from the Floridas this group of freebooters, among whom runaway Negroes will always find a refuge. It will, perhaps, be possible to have them received at St. Domingo, or to furnish them means of withdrawing from the United States!

	Florida Maroons , Chapter 1 from Freedom on the Border: The Seminole Maroons in Florida, the Indian Territory, Coahuila, and Texas by Kevin Mulroy
	Africans and Indians: A Comparative Study of the Black Carib and Black Seminole from Ethnohistory, vol. 37, no. 1 (Winter 1990) by Rebecca B. Bateman
	The Exiles of Florida; or, The Crimes Committed by Our Government Against the Maroons, Who Fled from South Carolina and ... from Readings in Black & White: Lower Tidewater Virginia by Joshua R. Giddings

  During the 1790s, runaways in Virginia and the Carolinas hid in woods and swamps during the day, and emerged at night to commit "various depredations" on farms and plantations.  By the nineteenth century, several thousands lived in the Great Dismal Swamp on the border between Virginia and North Carolina. Slaveholders often ran advertisements mentioning that the fugitives were heading there:

Bonaparte ran away last Christmas without cause or provocation. He is about six feet high and rather slim yet very strong, twenty-eight years old, not of very dark complexion, full eyes, large mouth, fine set of teeth, speaks fluently. I have received information that he is lurking about the Dismal Swamp. ( Southern Argus, April 16, 1852.)

Maroons and Laborers in the Great Dismal Swamp from Readings in Black and White: Lower Tidewater Virginia by Tommy Bogger

Maroons have been described as "some of the most hate-filled and angry slaves." Before fleeing, they had often committed acts of violence against their owners, overseers or other whites. Many vowed never to return to bondage. Joe, who murdered a slave owner in South Carolina, fled deep into the woods. He recruited others to join him and became the leader of a band of fugitives. He was then given the nickname Forest, as he had made the deep woods his refuge. A group of slave owners petitioned the State Senate in 1824, saying in part:

"[Joe] was so cunning and artful as to elude pursuit and so daring and bold ... as to put every thing at defiance.... Embolden [sic] by his successes and his seeming good fortune he plunged deeper and deeper into Crime until neither fear nor danger could deter him first from threatening and then from executing a train of mischief we believe without parallel in this Country."

Forest remained at large and was caught only when a former companion betrayed him and revealed his location. The maroon leader was shot in the forest where he had successfully lived free for more than two years.

The maroons or "outlyers," as contemporaries called them, maintained their cohesion for years, sometimes for more than a generation. They made forays into populated farming sections for food, clothing, livestock, and trading items.  Sometimes they bartered with free blacks, plantation slaves, and nonslaveholding whites, and in a few instances white outlaws joined them, although this was rare.

It is estimated that at least fifty maroon communities were active in the South between 1672 and 1864.